GB1422899A - S-heterocyclic derivatives of phosphine or phosphite gold mercaptides and anti-arthritic compositions comprising them - Google Patents
S-heterocyclic derivatives of phosphine or phosphite gold mercaptides and anti-arthritic compositions comprising themInfo
- Publication number
- GB1422899A GB1422899A GB3376374A GB3376374A GB1422899A GB 1422899 A GB1422899 A GB 1422899A GB 3376374 A GB3376374 A GB 3376374A GB 3376374 A GB3376374 A GB 3376374A GB 1422899 A GB1422899 A GB 1422899A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphine
- gold
- phosphite
- mercaptides
- chloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title abstract 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 title abstract 4
- XDGCJGXFGCYHEK-UHFFFAOYSA-N [Au+3].[O-]P([O-])[O-] Chemical compound [Au+3].[O-]P([O-])[O-] XDGCJGXFGCYHEK-UHFFFAOYSA-N 0.000 title abstract 3
- 230000002456 anti-arthritic effect Effects 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- 229910003771 Gold(I) chloride Inorganic materials 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000012298 atmosphere Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 1
- DCVQRCZEVHAMBN-UHFFFAOYSA-M chlorogold;diethyl(phenyl)phosphane Chemical compound [Au]Cl.CCP(CC)C1=CC=CC=C1 DCVQRCZEVHAMBN-UHFFFAOYSA-M 0.000 abstract 1
- LVTCZSBUROAWTE-UHFFFAOYSA-N diethyl(phenyl)phosphane Chemical compound CCP(CC)C1=CC=CC=C1 LVTCZSBUROAWTE-UHFFFAOYSA-N 0.000 abstract 1
- 239000010931 gold Substances 0.000 abstract 1
- 229910052737 gold Inorganic materials 0.000 abstract 1
- -1 gold halide Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 abstract 1
- 229950006389 thiodiglycol Drugs 0.000 abstract 1
- XYYVDQWGDNRQDA-UHFFFAOYSA-K trichlorogold;trihydrate;hydrochloride Chemical compound O.O.O.Cl.Cl[Au](Cl)Cl XYYVDQWGDNRQDA-UHFFFAOYSA-K 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/6541—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
- C07F9/65068—Five-membered rings having the nitrogen atoms in positions 1 and 3 condensed with carbocyclic rings or carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1422899 Phosphine and phosphite gold mercaptides SMITHKLINE CORP 31 July 1974 [1 Aug 1973] 33763/74 Heading C2P The invention comprises phosphine and phosphite gold mercaptides of the formula wherein R<SP>1</SP> is C 1 -C 3 alkyl, C 1 -C 3 alkoxy, phenyl, or phenoxy, X is -S-, -NH-, -N(CH 3 ]-, or -O-, R<SP>2</SP> and R<SP>3</SP> are H or together with the carbon atoms shown form a 1,2-benzo radical and = indicates an optional double bond. They may be obtained by reacting an appropriate triorgano phosphine (or phosphite) gold halide with an appropriate heterocyclic mercaptan, in the presence of alkali, such as NaOH, in a solvent, e.g. aqueous alcohol-chloroform, at about 25 C. for about 1 hour in a nitrogen atmosphere. The products have anti-arthritic activity and may be used as active ingredients in pharmaceutical compositions, especially those in dosage unit form. Diethylphenylphosphine gold (I) chloride is obtained by reducing gold acid chloride trihydrate to aurous chloride by treating with thiodiglycol saturated with NaCl and then adding diethylphenylphosphine in ethanol and stirring at 25 C. in an atmosphere of nitrogen.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US384666A US3883546A (en) | 1973-08-01 | 1973-08-01 | S-heterocyclic derivatives of phosphine or phosphite gold mercaptides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1422899A true GB1422899A (en) | 1976-01-28 |
Family
ID=23518252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3376374A Expired GB1422899A (en) | 1973-08-01 | 1974-07-31 | S-heterocyclic derivatives of phosphine or phosphite gold mercaptides and anti-arthritic compositions comprising them |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3883546A (en) |
| JP (1) | JPS5761035B2 (en) |
| BE (1) | BE818218A (en) |
| CA (1) | CA1054609A (en) |
| DE (1) | DE2437147C2 (en) |
| FR (1) | FR2240014B1 (en) |
| GB (1) | GB1422899A (en) |
| SE (1) | SE7409800L (en) |
| ZA (1) | ZA744598B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4165380A (en) * | 1977-02-25 | 1979-08-21 | Smithkline Corporation | Bis(sulfide)gold(1+) salts |
| US4172833A (en) * | 1978-03-20 | 1979-10-30 | R. T. Vanderbilt Company, Inc. | Process for preparation of 2-mercaptotoluimidazole and salts thereof |
| WO1985000747A1 (en) * | 1983-08-10 | 1985-02-28 | Stockel Richard F | Use of selenium-containing compounds for negating the toxic effects of gold compounds used in the treatment of rheumatoid arthritis, and a novel selenium-containing gold compound and use thereof as an anti-rheumatoid arthritis medicine |
| AU2015265715A1 (en) * | 2014-05-28 | 2016-11-24 | Auspherix Limited | Gold (I)-phosphine compounds as anti-bacterial agents |
| EP3148554A1 (en) * | 2014-05-28 | 2017-04-05 | Auspherix Limited | Gold (i)-phosphine compounds as anti-bacterial agents |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL131206C (en) * | 1965-09-03 | |||
| US3755329A (en) * | 1970-12-22 | 1973-08-28 | Du Pont | Nitrogen-heterocyclylgold(i) compounds |
-
1973
- 1973-08-01 US US384666A patent/US3883546A/en not_active Expired - Lifetime
-
1974
- 1974-07-18 ZA ZA00744598A patent/ZA744598B/en unknown
- 1974-07-26 JP JP49085967A patent/JPS5761035B2/ja not_active Expired
- 1974-07-29 BE BE147055A patent/BE818218A/en not_active IP Right Cessation
- 1974-07-30 SE SE7409800A patent/SE7409800L/xx unknown
- 1974-07-31 GB GB3376374A patent/GB1422899A/en not_active Expired
- 1974-07-31 CA CA206060A patent/CA1054609A/en not_active Expired
- 1974-08-01 DE DE2437147A patent/DE2437147C2/en not_active Expired
- 1974-08-01 FR FR7426773A patent/FR2240014B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU7180774A (en) | 1976-02-05 |
| CA1054609A (en) | 1979-05-15 |
| ZA744598B (en) | 1975-07-30 |
| DE2437147C2 (en) | 1983-03-03 |
| JPS5761035B2 (en) | 1982-12-22 |
| BE818218A (en) | 1975-01-29 |
| DE2437147A1 (en) | 1975-02-13 |
| FR2240014B1 (en) | 1978-07-21 |
| US3883546A (en) | 1975-05-13 |
| FR2240014A1 (en) | 1975-03-07 |
| SE7409800L (en) | 1975-02-03 |
| JPS5041859A (en) | 1975-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |